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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 02:57:39 UTC
Update Date2019-11-12 17:21:36 UTC
HMDB IDHMDB0128430
Secondary Accession NumbersNone
Metabolite Identification
Common Name14-(acetyloxy)-3,5-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11,13,15-heptaen-13-yl acetate
Description14-(acetyloxy)-3,5-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11,13,15-heptaen-13-yl acetate belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. 14-(acetyloxy)-3,5-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11,13,15-heptaen-13-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). 14-(acetyloxy)-3,5-dihydroxy-9-oxo-8,17-dioxatetracycloheptadeca-1(10),2,4,6,11,13,15-heptaen-13-yl acetate is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 14-(acetyloxy)-5-hydroxy-9-oxo-8,17-dioxatetracycloheptadeca-1(10),2(7),3,5,11,13,15-heptaen-13-yl acetate. This aromatic-hydroxylation-of-fused-benzene-ring-pattern3 occurs in humans. It is generated by cyp1a2, cyp2b6, cyp2c8, cyp2c9, and cyp2c19 enzymes via an aromatic-hydroxylation-of-fused-benzene-ring-pattern3 reaction.
Structure
Data?1563875386
Synonyms
ValueSource
14-(Acetyloxy)-3,5-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2,4,6,11,13,15-heptaen-13-yl acetic acidGenerator
Chemical FormulaC19H12O9
Average Molecular Weight384.296
Monoisotopic Molecular Weight384.048131966
IUPAC Name14-(acetyloxy)-3,5-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-13-yl acetate
Traditional Name14-(acetyloxy)-3,5-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0^{2,7}.0^{11,16}]heptadeca-1(10),2,4,6,11,13,15-heptaen-13-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)OC1=C(OC(C)=O)C=C2C(OC3=C2C(=O)OC2=CC(O)=CC(O)=C32)=C1
InChI Identifier
InChI=1S/C19H12O9/c1-7(20)25-13-5-10-12(6-14(13)26-8(2)21)27-18-16(10)19(24)28-15-4-9(22)3-11(23)17(15)18/h3-6,22-23H,1-2H3
InChI KeyIAFINIRBOYVOPV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassCoumestans
Direct ParentCoumestans
Alternative Parents
Substituents
  • Coumestan
  • Angular furanocoumarin
  • Furanocoumarin
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Furopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Furan
  • Carboxylic acid ester
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.1ALOGPS
logP1.61ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)6.6ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area132.5 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.88 m³·mol⁻¹ChemAxon
Polarizability37.12 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-3000900000-2f3ba534166978f7635cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-4029000000-9dea445c8be2f9d3b058Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002u-0009000000-6d63de8b1e00a4917ed0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004l-0009000000-731815994715a235a7d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-005d-2097000000-def9bf041d95b96f56e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-0009000000-5ce840b6093121a83e3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0029000000-b9dc1b0b91163142aceaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-6091000000-033d4ca58b76c2c5c7ddSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131834770
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.